Crowdsourcing my wardrobe (help me dress like an adult)

Ok, this post is going to be a bit weird, but I need your help. I’m 26 years old, but I feel like I still dress like I’m 16. I hate clothes, including shopping for them, taking care of them, selecting them in the morning, etc. As a result, I often just throw on a pair of jeans, one of the five shirts that I’ve had for years, and a hoodie. However, I’m getting tired of this. Previous attempts to improve my wardrobe have not gone over well, so I’m turning to the public at large for help. I know I can’t be the only guy (or girl) out there who wants to dress better but is completely lost as to where to start. I’d absolutely love any advice, from people who struggle with it, and from people who love clothes and fashion. But first, here’s a bit of background about the context of the problem:

My activities

Everyday
I’m a web developer / entrepreneur, so I spend a good portion of each day working from home or from my neighborhood coffee shop. I would like to look halfway presentable during these times, but comfort is a key factor here.

Professional meetings
As part of my work, I often have to meet with clients and potential partners. Obviously, this requires a bit more decorum than sitting alone at home does, but this is San Francisco, so I don’t need to show up in a suit or anything. Perhaps a button-down and a sweater when it’s cold?

Casual evenings out
Dinner with family, accompanying my wife to a play, grabbing drinks with an old friend. I don’t need to wear a tie, but perhaps a blazer or something?

Formal affairs
Weddings, funerals, very special occasions, etc. I have a good dark suit, so I’m pretty much set here, I think.

My criteria for clothes

Flexible
I don’t have a lot of cash or space, so it’s important to get staples that can be paired into as many combinations as possible. I’d rather not buy an item of clothing that can only be worn with one other item of clothing, for example.

Affordable
I’m willing to spend some money here, but I’m not paying more than $100 for a pair of jeans, for example. I’m willing to spend more for great articles of clothing that will last years and fit with a lot of situations.

Durable
I hate clothes that shrink in the dryer, get stretched out after just a few times of wearing them, fade easily, etc. I’m looking for good stuff that will last awhile. I’m also looking for classic items that are durable in the sense that they won’t go out of style in six months. I think guys have it easier here, fortunately, but there are still fads that I want to avoid, at least for the most part.

Comfortable
If I’m not comfortable in my clothes, I won’t wear them. I’ll revert back to my jeans and tshirt “style”, which is not what I want. Not sure what people can suggest here, but there it is.

Easy to take care of
I hate to iron. Seriously, anything that doesn’t require me to iron it for twenty minutes has a huge advantage. If I can just throw it in the washer and dryer without worrying about ruining it or having it shrink, that’s a big plus. I’m willing to do some work to take care of things, but I’m not sure I’m into hand-washing and line-drying all my clothes.

What I need help with

What to buy (and what NOT to buy)
What are the absolute essentials? What are some ideas for good combinations that fit the criteria above? What should I not buy…are sweater vests still awesome? 🙂 Something like this, for example:
– 2 pairs of jeans
– 2 pairs of dress slacks
– 4 button-down dress shirts (2 dark, 2 light)
– 2 sweaters (1 dark, 1 light)
– 2 pairs of shoes (black dress shoes, brown casual shoes)
– etc, etc.

Where to buy it
Should I be looking at Brooks Brothers, Old Navy, Macy’s, Wal-Mart, Banana Republic, or some funky thrift store? Ok, a couple of those were jokes, but seriously…what kinds of stores are great to find what I need? Links to online stores are definitely appreciated.

How to buy it
Is it worth waiting for sales? Should I be more opportunistic and buy stuff that strikes my eye, or should I come up with a plan and stick to it? Should I only buy stuff that fits perfectly, or should I consider buying and having things tailored? Which kinds of clothing work well with that strategy, and which don’t?

Other resources
Good books, blogs, or sites that are geared towards helping young professionals dress appropriately in a variety of social situations. most of the books I’ve looked at for men’s fashion were clearly written for people who are trying to decide what combination of tie and dress shirt to wear with their suit every day. I need to wear a suit perhaps once or twice a year. Links to particular articles of clothing would also be interesting. Even TV shows or movies where you like the wardrobe styles would be helpful at this point.

This post turned out a lot longer than I had envisioned. I was just thinking I’d ask for a bit of advice. Am I being too…structured here? I really want to get better at this area of my life, so I welcome any and all suggestions. Please post something in the comments…I’d really appreciate it. Thanks!